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Although ethyl bromide and isobutyl bromide are both primary halides, ethyl bromide undergoes SN2 reactions more than 10 times faster than isobutyl bromide does. When each compound is treated with a strong base/nucleophile (EtO-), isobutyl bromide gives a greater yield of elimination products than substitution products, whereas with ethyl bromide this behavior is reversed. What factor accounts for these results?
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Based on our data, we think this problem is relevant for Professor Hopkins' class at UW-SEATTLE.
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Our data indicates that this problem or a close variation was asked in Organic Chemistry - Solomons 10th Edition. You can also practice Organic Chemistry - Solomons 10th Edition practice problems.